These people have gone all-in on boat life. Here’s how they did it

Imagine casting off most of your worldly possessions to live on a sailboat you bought on the Internet – perhaps without even seeing it, or knowing how to tie a knot or hoist the mainsail. For some newbie sailors who embarked on boat life during the pandemic, the past year provided an unexpected push to make what may have once seemed unattainable suddenly within reach. Randi Hitchcock was 30 days into lockdown last April with her family in Colorado Springs, Colorado, when she hit the wall. “The hours upon hours we had been sitting in the house when we weren’t walking our dogs on an essential trip to the park made us think long and hard about our future,” says Hitchcock. After a few family discussions with her husband, Steve, and their then 12-year-old son, Cody, the Hitchcocks decided to sell most of their things, put their house up for rent and head to St. Augustine, Florida. There, they moved onto the 38-foot catamaran, Konstantina, that they bought “sight unseen” for roughly $125,000 off Facebook. The family had no sailing experience. But thanks to the G.I. Bill, Steve, a veteran, was able to take free American Sailing Association classes and Professional Mariner Training in the Florida Keys and Stuart, Florida. The Hitchcocks spent several months sailing in Florida before crossing to the Bahamas in mid-February of this year, where they have since logged some 400 nautical miles. When their Bahamian visa expires in May, they plan to return to Florida to live in a marina or at anchor so Cody can attend in-person high school this fall. And while Steve’s VA pension can support the family, he might pick up jobs delivering boats and Randi might work in a marina store for discounts on boat parts, she says. One thing’s for sure, says Hitchcock – as soon as they can, they’re putting their Colorado house up for sale. “I don’t think we have any desire to live in a house again knowing how easy and fun it is to travel on a boat,” she says. Boat life is booming Life the van life movement that exploded in recent years – and even more so during the pandemic – boat life is not new. It is, however, trendy. Popular sailing YouTube channels like Sailing Ruby Rose and Sailing SV Delos, among many others, feature attractive couples and families covering their living expenses (and often far more) with YouTube ad revenue, paid sponsorships and support from Patreon – a subscription-based crowdfunding platform used by content creators to make money. And like RV sales during the pandemic, boat sales, too, have boomed. “The pandemic has had an incredible effect on the purchase and chartering of yachts of all sizes,” says sales and charter broker Mark Elliott, of the International Yacht Company. “In my over 40 years of yachting, I have never seen the market so active.” “We are selling all size yachts and the inventory has shrunk to an all-time minimum,” he says. According to the National Marine Manufacturers Association, the US recreational boating industry saw an increase in first-time boat buyers in 2020 for the first time in over a decade. One couple’s transition from van life to boat life Maggie Jay and Damien Williams, who are digital nomads working in marketing and finance, are among those first-time boat buyers diving right in. The Denver, Colorado, couple made a brisk transition from RV life to boat life after an accident claimed their beloved motor home. After four years traveling across 35 US states in a 1974 GMC Painted Desert motor home that Jay says “looked like a stretch Scooby Doo van,” an engine fire in 2019 put an end to the adventure. “We had restored it ourselves, it was heartbreaking for me,” says Williams. “I didn’t want to start all over again with a new motor home. I just wanted to do something different.” He’d always been intrigued by sailing but thought it was something you had to grow up doing – or at least have a lot of money to afford, he says. When he proposed the idea of living on a sailing boat to Jay, she says she imagined it like “rough camping on the water.” “I just kind of heard stories from my aunt and mom, who sailed, about peeing in a bucket and cooking on a Bunsen burner,” she says, “I was wondering how that worked for something more than a weekend.” She soon found out. In late February 2020 – after checking out roughly 20 boats while driving along the Gulf Coast from Texas to Florida with their schnoodle, P-Moe – the family found their new home. They bought their 1979 Pearson 35 (which they plan to christen Sailing Dipity) for $12,600 in Dunedin, Florida. With pandemic lockdowns just starting as they were settling into life at anchor, Jay and Williams learned to sail by watching a lot of YouTube videos and sailing channels, poring through books and bartering Maggie’s shed-organizing skills for sailing lessons from a captain they met. By mid-April of this year, after logging hundreds of nautical miles while learning to sail around Florida, they crossed from Miami to Bimini in the Bahamas and plan to arrive in Puerto Rico by January 2022 for their wedding day “Even compared to life on land in the motor home, I’ve never felt so much privacy and freedom,” says Williams. “On land in an RV, you’re always worried if someone will bother you, if you’re parked okay.” “All over the world we can anchor for free, it feels really freeing,” he says. Is it for you? As glamorous as the sailing liveaboard life can look on YouTube and Instagram, not everyone is cut out for it. And just as there are coaches for nearly everything these days, there are sailors who specialize in helping people figure out if living on a sailboat might be for them. Sailing Totem offers “mentoring, guidance, resources, and practical support to help YOU make a successful transition into the cruising life,” according to its website. Jim and Judy Brown of Sail Dauntless invite would-be sailors aboard their 55-foot Jeanneau sailing yacht (based out of Sag Harbor, New York this summer) to “get soaked and go sailing for a week with a seasoned crew with offshore and island hopping itineraries” while experiencing the realities and rewards of a liveaboard lifestyle, Jim Brown wrote in an email. After that, if guests are still interested in the boating lifestyle, Brown says, the next step is to hit the books to study and get certified to safely operate the specific type of sailing yacht that sparks their interest. A common misperception for people new to the sailing lifestyle, he says, is that you’ll “glide along to your next destination with fair winds and calm seas.” And that doesn’t only apply to changing weather. “People do not realize how expensive this lifestyle is, even with prudent budgets,” Brown says. Even ordering a simple repair part that might cost $15 online could cost many times that by the time it’s gone through customs and processing fees, he says. New sailors might also be surprised by how long it takes to get places on wind power. “If man could walk on water, it would be a better option if you are in a hurry,” Brown says. “Most sailing yachts average five miles an hour, so patience is key.” A slower lifestyle can be a reward For families who like the idea of a slower, more minimalist way of living (and don’t mind close quarters), the liveaboard sailing lifestyle can be appealing. Jessica and Will Sueiro, who run a travel coaching company, WorldTowning, to help people navigate the logistics of longterm travel, recently decided to embark on liveaboard life with their two children, Largo, 13, and Avalon, 16. The family had been traveling full time since 2014, homeschooling the kids while visiting every county in Europe in an RV (among other adventures) before landing in Japan in late February 2020. Living on a sailboat was always part of their “endgame,” says Jessica, and the pandemic accelerated that. “We realized that Covid was going to go on much longer than we all originally anticipated,” she said in an email. “And the desire to take on a project while we had to pause travel seemed like the perfect opportunity for our family to learn how to live on a boat and sail.” In August 2020, after returning to Europe, they bought their sailboat, S/V Friendship, a Broadblue 38 catamaran, for around $160,000 in the South of France and have been learning to sail it since. The family plans to cruise around Spain’s Balearic Islands this summer before sailing across the Strait of Gibraltar to Morocco. “There is a huge learning curve if you have never sailed before,” Jessica says. “Hire an instructor, crew on other boats, hire a coach, read books, attend boat shows, pick brains, watch YouTubers, take specialized classes in CPR/navigation/weather/engine repair and more.” And don’t forget to tap the vast sailing community in port, at anchor and at sea. “Other than social media friends, we didn’t experience much community in the van and RV life at all,” says Williams. He thought transitioning to sailing life from RV life would “be a lateral move,” he says, and has been surprised to find it an upgrade. “Sailors have been so generous, helpful and friendly toward us, even though we had never sailed a day in our lives when we moved on our sailboat,” he says.